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How to Correctly Date Multiple People at the Same Time

Dating is really just a string of dicey etiquette questions, but how do you talk to the person you’re dating about the other people you’re dating? Do I disclose at all? How do I divvy up my time? What do I say to a partner when things are starting to get more serious with that other person? With online dating becoming more and more popular, it’s only going to become increasingly common to see these questions come up, and, honestly, they should! I talked to people who are living/have lived the three-Internet-dates-a-week life, and distilled their advice into some basic rules of thumb.

Everyone Is Doing It This is less of a rule and more of a fact to keep in mind: That guy you’re on your first date with is on his fourth first date this month, and so are you. My friend P (and no, her real name is not just a letter but if you’re friends with P, then you’re friends with me) put it best. “Assume people are sleeping with other people unless they ask or say otherwise,” she says. This might seem like a sort of defense mechanism against getting too involved, but I like to think of it more as a liberation tool—you assume that they’re sleeping with other people, they assume that you’re doing the same, and all of a sudden the pressure is off this date. You’re my third option right now! And, more importantly, I’m your third option! You’re not hanging all your hopes on this coffee right now either? Great, now we can finally interact as humans.

Keep Your Dates on a Need-to-Know Basis As P puts it, “Don’t feel guilty about seeing more than one person, because you can make it weird, and don’t overshare about more than one person.” If they ask you what you’re doing on Saturday, tell them you are “busy.” If they ask what you’re doing, tell them you’re “meeting up with a friend.” If they ask which friend, defer, or lie. And don’t, under any circumstances, bring it up yourself. That’s just an issue of common courtesy. When you’re on a date with someone, they deserve your undivided attention. Maybe, more importantly, they deserve to feel like they have your undivided attention.

It’s Not What You Say, It’s How You Say It Most people you meet are prepared for you to do something shitty to them. Shitty things happen all the time. But there’s a big difference between a bad thing done poorly and a bad thing done well. L, a friend I can only describe as having advanced degrees in the science of online dating, says, “My personal experience is that people don’t worry about what is happening as much as they do how it is happening. It might be sucky that you’re not going to be free for the next week, but it is good that you responded to the text quickly. People are generally equipped to handle bad events better than they handle bad attitudes or treatment.” It’s unavoidable that you’re going to let some people down. But a little consideration, some warning ahead of time, an acknowledgement of fault, and a sincere effort to protect the people around you will go a long way.

Be in the Moment Think of dating less as an iterative process for finding someone perfect and more like a series of potentially enjoyable evenings with beautiful strangers. For a large stripe of people, especially in cities, dating one person at a time is uncommon, if not completely fictional. But even if I’m seeing 40 women, at any given moment, I’m with only one of them. And if you find yourself thinking about one person you’re seeing even when you’re with the others, well, that’s a good problem to have.